(Bloomberg News) Even if John Paulson persuades Hartford Financial Services Group Inc. to break itself up, the hedge fund manager could still come up short in his billion-dollar bet on the 201-year-old insurer.

Hartford's biggest shareholder said this week he may seek support from investors for a plan to split the property-casualty and life-insurance businesses, pushing the stock to a six-month high yesterday. Hartford, which sells for less relative to net assets than comparable U.S. insurers, according to data compiled by Bloomberg, could be worth $32 a share by separating the units, he said. That's 50 percent more than its current price.

Paulson, who had his worst year on record in 2011 after making billions of dollars from anticipating the collapse of the U.S. subprime market, needs Hartford to reach about $24.71 a share to recoup his investment, filings to the U.S. Securities and Exchange Commission and data compiled by Bloomberg show. While Dowling & Partners said regulatory hurdles and Hartford's debt will ultimately prevent a split, even a successful breakup may only boost the insurer's price to $25 a share, according to FBR & Co. and Stifel Nicolaus & Co.

"I just don't see how that happens," Dan Theriault, a New York-based analyst at Portales Partners LLC, said in a telephone interview, referring to Paulson's estimate for Hartford's breakup value. "These things, while they look good on paper, really from a reality standpoint don't create the value that you'd think," he said.

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Armel Leslie, a spokesman for Paulson, who runs the $23 billion hedge fund Paulson & Co. in New York, declined to comment on whether the Hartford investment would be profitable.

Shannon Lapierre, a spokeswoman for Hartford, based in the Connecticut city of the same name, declined to comment on whether breaking up the insurer would boost returns for shareholders and referred to its Feb. 14 statement.

In it, Hartford said "there are potential benefits to a separation," while it also recognized there are "challenges to successfully executing a separation."

Founded in 1810, Hartford sells savings products and life insurance policies that compete with those from firms such as MetLife Inc. and Prudential Financial Inc. Hartford's rivals in the property-casualty market include Travelers Cos. and Berkshire Hathaway Inc.'s car-insurance unit Geico Corp.

Once worth more than $33 billion in 2007, Hartford plunged 96 percent to its low in March 2009 as the worst financial crisis since the Great Depression produced losses on equity- linked variable annuities the insurer sold in the U.S. and Japan, often with guaranteed minimum returns for customers.